Just over a year ago, Steve Dubbeldam founded Wilderness Collective, an adventure-based service offering men unique experiences to leave their day-to-day lives behind and step into the unknown. Lasting a few short days, the trips—while brief in duration—take on an extended life of their own. From climbing Washington state's Mount Baker to horseback riding in the Sierras, the rugged trips may not be best suited to amateur outdoorsmen but with varied types of outings, how hard you rough it is up to you—and on each trip, incredible freshly made meals and artisanal coffee and cocktails await each sunrise and sunset. Each trip is a comprehensive package; guaranteeing both a list of essential gear before and wealth of stories to tell after the fact.

Hot off the completion of our very own cross country motorcycle ride, we jumped at the opportunity to join early October's WC-005, a dual-sport ride through the Sequoia National Forest to Yosemite National Park. The four-day trip was as transcendental as promised—all thanks to some lucky breaks in weather, a group of freewheeling Georgia boys and a contagious feeling of excitement that not even a few hard falls could shake.

Rather than recap the singular experience we chose to speak with Dubbeldam himself on the spirit of Wilderness Collective, lessons learned and just what makes his trips tick.

How did you come up with the Sequoia-to-Yosemite trip route?

The motorcycle trip came from a scouting trip. I bought a dual-sport bike and I was like "Man, it would be awesome to if there was a way to ride from LA to Yosemite all off road." After riding through [south end of Sequoia], it was literally just like, "How did I not know about this? I have to take people here." It was just too amazing.

Same thing with the Channel Islands trip. First time I did that, I bought my catamaran for $500 on Craigslist, and a friend and I took it. We literally bought a compass from RiteAid, drove up to Oxnard and sailed across the busiest shipping lane in CA to an island in marine fog. It was very, very ill-planned. But that trip sparked this real feeling of exploration and adventure in me that I hadn't felt since I was a kid. And that's what I'm trying to essentially capture and give people. You know, I jumped off the dock onto the boat and was like, "Oh man, I don't know what I'm getting into."

Is that what you're after with Wilderness Collective then? Finding that feeling of adventure?

It's such a rare feeling that I think there's less and less opportunity for that as we get older. You know, I grew up on 40 acres, and when I was a little kid going past our fence line (which I wasn't supposed to do) I'd get that pit in my stomach and feel like, "Alright, now I'm on an adventure."

And obviously it's not like sailing to the Channel Islands is charting out an island that nobody knows about, but it's still sailing out there in a tiny boat. It's still a feat. You know, it's rugged. But I don't want it to be adventure for adventure's sake. I want it to create the context for people to grow, whether it's personally or in relationships or even push themselves physically to do things that are scary for them, things that are hard for them. But I'm also just as happy—if not happier—if somebody buys a dirt bike instead of coming on one of my trips. I'm happy if guys are getting out there and making adventure a priority because I found personally that it brings a huge level of balance to your life.

Most the trips are of relatively short duration. Why not set out for an extended stay?

I try to make the trips a pretty compressed experience that fits into a weekend or a few days, [that way] it holds people completely out of their normal element. So that's why, on the bike trip, we sleep in tents instead of staying in little lodges. And the packhorse trip was really cool for that because it's an immersive experience—you ride out for one day all the way deep into the woods, and then you're just there for five days.

And as much as possible I really like to do A-to-B destination based trips. Then it gives you that sense of urgency like, "I'm not sure we're gonna get [there]." On the last night of our trip, we all rolled up in the dark—you know, it makes it feel a little more intense.

Some guys on WC-005 suggested getting individual maps. What do you think of that?

Yeah, that's interesting because I've thought about this. I mean, there's a reason I don't have a map. There's a reason I don't give every guy a little GPS unit on his bike. I just try to work at every different angle to help guys actually be present in the experience. That's why I was like, "No cameras, no phones." Because I think our instinct is to want to quantify everything and know where we are, know what's gonna happen next, know how close we are to [the next] point. Even having a map—you're thinking about where you are in relation to the map. You're not just thinking, "I'm just here and this is beautiful."

Have you been surprised by an certain demographic or type of guy that Wilderness Collective has attracted thus far?

In terms of unexpected clientele, I think what I didn't anticipate—which has been an awesome thing—is like the whole father-son vibe. Yet it's awesome to have older guys on these trips. Just the way they talk about things is different. They've got different insights, different opinions.

I think it's the classic thing with guys; we bond or grow closer together doing a shared experience, shoulder-to-shoulder—I think that's true. I've found that even creating a context for that kind of stuff to happen is amazing. It just lets people kind of connect, whether it's to themselves or with another person. I've had all different kinds of people on trips, but the common thread is that they all had some kind of deeper experience that they didn't anticipate. Every single trip by the end of it guys are hugging, sharing contact info. It's like, "I love you, man!" It's like summer camp.

Do you think this is influenced by removing technology from the situation?

Yeah, I think it helps. You know, for some people, giving up the phone is the hardest part—which is crazy. But I catch myself doing this too; whenever you have a second of downtime you pull out your phone and you look for some kind of stimulus. Whereas if you don't have that you're forced to either think about something, or to think about nothing, and soak it in. So I think it naturally lends to higher levels of introspection and just lets your thoughts kind of roll around in your mind. It's giving people a break, like, by the end of the trip you're not really thinking about the stressful email or this or that. And the big reason too is; I just don't want people to be obsessed with taking photos. I just want them to be having a great time.

Looking back on six trips completed, can you put a finger on the biggest thing you've learned so far?

I want people to leave the trips feeling a little different. I want it to be this pretty powerful experience. Not just, "Oh, that was a cool trip. Time to go back to my normal life." So that has been the biggest learning curve for me—learning the questions to ask, what are the questions not to ask. I didn't want this to be like leadership weekend where I'm giving talks every night around the fire and that kind of thing.

Yet I think every trip I've been on, there have been incredible conversations that've been really deep, meaningful stuff. So for me the biggest learning curve is figuring out how much of that do I need to push and how much of it do I just need to literally leave to the trip—the adventure, the camaraderie, the side conversations that I'm not even a part of. And I think that I've learned that actually just providing that environment for guys to be in—a lot of that stuff, the deeper stuff, actually just happens naturally.